Business is like the game of Poker
Every poker player knows the most dangerous hand in the game. It is not the weak hand — a weak hand costs you a small bet and an easy fold. It is the strongest hand at the table, played by a man who has stopped paying attention. Pocket aces do not play themselves. They only look that way, right up until the board runs out against the player who assumed the pot was already his. Sears, Roebuck and Company held pocket aces for the better part of a century, and lost the hand anyway.
Count the cards Sears was holding. Its catalog reached farms and small towns that no store could serve, and it sold everything a family could want — clothing, tools, appliances, and, for a time, entire houses shipped as kits and assembled on the buyer’s lot. Sears had invented remote retail generations before the internet existed: the customer ordered from a book, and the goods arrived by rail and mail. Later its department stores anchored the suburban shopping malls of postwar America. Brand, scale, distribution, customer relationships, the trust of ordinary families — Sears held every good card there is, all at once, for decade after decade.
I grew up in the world Sears built. The catalog was furniture in American houses, and the Christmas Wish Book arrived each fall like a second holiday. In my years practicing law and developing land, I watched towns rise around malls that Sears anchored; a signed Sears lease was the signature that made a shopping center financeable. Nobody I knew imagined that company could fail. That is precisely the point. Nobody inside it seems to have imagined it either.
The cards were never taken away. Read the record carefully and you will not find the hand where Sears lost its brand or its distribution to a stronger player. What happened is slower and sadder: the game changed, twice. Walmart’s discount stores took the price-conscious customer in the late twentieth century, and online retail took the convenience customer in the twenty-first. Sears answered neither change with the assets it already owned. A company that had grown comfortable with its hand stopped playing it — stopped widening the moat, stopped asking what the next game would reward — and in 2018, more than a century after its founding, it filed for bankruptcy.
Here is the irony that should keep every comfortable business owner awake. Of all the companies on earth, Sears should have owned online retail. It had the catalog — which is to say, the product knowledge and the merchandising skill. It had the warehouses and the delivery relationships. It had millions of households who already trusted it to sell them things they had never touched. The internet store was, in substance, the Sears catalog rebuilt for a new medium. Amazon built it instead, starting from nothing, while the company that had run that exact business for a hundred years watched from the rail. Sears did not lack the cards. It lacked only the willingness to play a familiar hand in an unfamiliar game.
The lesson is not really about retail. Good cards make players careless, in poker and in business alike, because an advantage you have always held becomes invisible — you stop seeing it as a position to defend and start seeing it as a fact of nature. But a moat is not a fact of nature. It is a ditch that silts up unless somebody keeps digging. The companies that kept their advantages longest acted as though those advantages were temporary, because they are. The game always changes: a new technology, a new competitor, a new customer habit. The only question is whether you will play your strong hand in the new game or keep betting it in the old one.
Here is the takeaway. Write down the strongest cards your business holds — the brand, the location, the customer list, the cost advantage, the reputation — and then ask the Sears question about each one: if the game changed tomorrow, would this card still play, and am I playing it, or merely holding it? Holding is not a strategy. A strong hand raises its owner exactly one obligation, and it is not gratitude. It is attention. Play your aces like they can lose — because seated across from a changing game, they can.
